Yeah, I also think Orlando went into that series with the better roster. Nick Anderson is a punch line now (thanks to game 1 of that series) but at the time he was a very well-regarded shooting guard and Dennis Scott was a perfect complementary player, with his spot-up three-point shooting.
I hate playing pop psychologist, but I think Orlando lost a ton of confidence after letting Game 1 slip away when it was basically as in the bank as a close-ish game can be. However, while I think it's fair to say that Orlando underperformed in that series and Houston overperformed, I don't think it's fair to say Shaq underperformed. It's popular wisdom to say that Olajuwon dominated Shaq, but that's really not true. Olajuwon was a greater force than their respective stat lines suggest and I wouldn't argue those who say Olajuwon played a better series, but Shaq was insanely productive. He wasn't the problem.